How to Play the Devil's Advocate (Without Being Evil)

This is a delicate endeavor. Voice your opinion too fervently, and
you risk offending your colleagues
or squashing a good idea that could develop later. But, say nothing, and the idea could easily veer way out into left field—leaving feelings intact, but also leaving you worried about the fate of your team or company.

In these types of situations, it’s no surprise most of us hedge our feedback by blaming our favorite red-tailed villain before voicing our opinion, starting the conversation with, “I’m just playing devil’s advocate.”

And yes, that little devil can be your friend—if you know how to use him. After all, being the dissenting voice your team needs requires a bit more strategy than a one-liner. So here are a few guidelines for playing devil’s advocate—without coming across as an evil mastermind.

Know When to Play the Part

If Hollywood has taught us anything, it’s that you don’t mess with the Prince of Darkness unless you’re prepared to handle the consequences. Before you can play devil’s advocate in the office, you first need to seriously consider whether or not it’ll be worth it. There are some situations where no amount of help—nefarious or otherwise—will do anything but piss off your colleague. Playing the other side with your boss, for example, should be approached with extra care (and I don’t recommended it for novice debaters).

So before you engage the strategies below, first consider the worst-case scenario. How receptive is this colleague to feedback, based on past experience? Is she likely to
go completely off the rails
when she realizes you’re poking holes in her idea? How might your challenge impact your working relationship with her or with your team? And what will your boss think when he or she hears about it? Try to imagine how the conversation could go wrong, and weigh that against the importance of the topic at hand.

If you do decide to play devil’s advocate, then your next step isn’t to say anything—it’s to to start listening.

Listen

Before you can justify disagreeing with someone’s idea, let her fully lay it out for you first. That means: Sit down, pay attention, and make sure the idea-sharer knows you’re hearing her. Establishing that connection reinforces respect, and will make your colleagues
much more receptive to feedback
later on.

As you’re listening, try to find ways you actually agree, whether it’s in process or intent. Finding any common ground will help soften any feedback you give later on, and show that you’ve taken the time to consider the idea from every angle.

Just think like your eighth-grade English Lit teacher told you, and tell yourself there are no dumb ideas. At least—not at first.

Test in Real Life Situations

Even if you’re positive an idea has no legs, the person sharing it obviously thought it did, so after you’ve heard all the nitty-gritty, ask how the plan would play out in real life.

For example, if someone has an idea to increase productivity by corralling the team into a communal table in the middle of the office, ask how certain aspects of business would be impacted by the change. What happens if a client calls and the rest of the team is in the midst of a heated debate? What about confidentiality and privacy?

By allowing your colleague to walk you through her vision of how various real situations would be handled, you not only confirm that she’s considered those potential snags (or not) but you allow her the chance to discuss the challenges without coming right out and telling her you don’t agree.

Also, don’t forget to keep an open mind during this stage. Playing the devil’s advocate to someone else’s ideas also means you need to apply the same standards to your own. Give ideas an honest chance, and test out your own assumptions, too. You just might discover that the idea has merit, after all.

Stay Positive

French poet
Charles Baudelaire
once wrote, “The devil’s finest trick is to persuade you that he does not exist.” That’s pretty much what you want to accomplish if you’re playing the part yourself. That means, even as you’re disagreeing with someone, you should keep your tone positive and encouraging, and try to emphasize that your goal is to address the problem as a team—not just to shoot down an idea.

Practically speaking: Before you give your feedback, try to find something meaningful (but not too benign) about the idea and comment on that. This is where having that common ground comes in handy. For example, if you were trying to persuade the CEO of Yahoo! not to force all the staff working remotely to
give up their freedom and work at the corporate headquarters
(hypothetical, of course), you could point out that you “appreciate the sentiment behind having the entire team under one roof to help foster collaboration.” Then proceed. Make it clear you’ve listened to the idea with an open mind, and she’ll be much more receptive to your point of view.

Don’t Beat a Dead Horse

That said, once you’ve made your point, don’t dwell. If everyone has come to your way of thinking as a result, fantastic, but nobody appreciates a gloater. If, however, you’ve failed to sway everyone in the room, the same strategy applies. Give it a rest and let everyone marinate on the topic for a while before bringing it up again. Remember, if you haven’t convinced them yet, hearing your thoughts seven more times probably isn’t going to do the trick. You’ll need a much stronger argument—or to simply admit defeat. (Unfortunately,
you can’t win them all
.)

Whether you believe in a red-faced villain with horns and a tail or not, when it comes to playing devil’s advocate, the mayhem that could ensue if you don’t play the part with care is as real as your paycheck, and it should be handled with that in mind. But, when done right, playing devil’s advocate can not only help advance your own ideas, it can build trust and strengthen your relationship with colleagues and help you all reach a better solution to the problem at hand—all without actually being evil.

Jennifer Winter is a freelance writer, editor and career consultant. She translates her 14-years of corporate combat experience to help others navigate their own careers, and become advocates for their own success. Need help negotiating that raise or writing the perfect email to your boss? Jennifer’s your girl. Find out more about her services on her blog, FearLessJenn or follow her on Twitter @fearlessjenn.

Meet The Author

Jennifer Winter is a freelance writer, editor and career consultant. She translates her 14-years of corporate combat experience to help others navigate their own careers, and become advocates for their own success. Need help negotiating that raise or writing the perfect email to your boss? Jennifer’s your girl. Find out more about her services on her blog, FearLessJenn or follow her on Twitter @fearlessjenn.